Situated in the lesser-traveled part of southwest Scotland, Glenapp Castle offers a charming alternative to the often-overcrowded Highlands. The 19th-century baronial property was purportedly used by Winston Churchill in his planning of the D-Day landings, a pivotal turning point in World War II. At 4,500 sq ft, The Castle Penthouse Suite is one of the biggest hotel rooms in Scotland and offers beautiful views of the Isle of Arran and Paul McCartney’s beloved Mull of Kintyre. The four-bedroom suite occupies a whole floor and has its own elevator. It also has a sauna, game room, library, and a private dining room for up to 16 guests. For a family trip to remember, book the Hebridean Sea Safari, which takes guests around the biggest and best islands including Islay and Jura, where dolphins, whales and puffins will likely join you.